Don’t Rush Into Your Side Hustle with Scott Leese

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What up, everybody?

Welcome to another episode of the live Better Sell Better podcast. This is your host, Kevin Dorsey, AKA kd. And today I could not be more excited not only for the topic, but also for the guest, because from a topic perspective, we are going to be diving into on how to break the dependency on your W2 job. How can you make additional income on the side? How can you get multiple income streams coming in to support your lifestyle, your family, and ideally your goals? But the person that's going to talk about this is probably the best person out there to discuss it, which is my good friend Scott Lease, because he's done it. He has lived it, he has executed on it, he has done things well, he has made some mistakes, he has learned, and he's continuing to teach these lessons to everybody else out there. So Scott and I are going to be diving into how do you break the chain? How do you become untethered in Scott's language to generate income and ideally eventually not be dependent upon your W2 for your income stream? So, Scott, my man, welcome back to the show. Let's do this, man.

What's up, Kevin? Good to be here, man. Thanks for having me.

So. So let's, let's talk about this. And the first question might be taking it a different direction, but this idea, you know, right now it's like everyone's trying to be a consultant. Everyone's coming out with a course. Everyone's, you know, like, ooh, I hit quota course consulting. When should you consider starting to sell your services or knowledge? Like, what. What things should lead up to? What? Finally deciding, hey, I should maybe start to charge people for the information that I have in my head.

The tipping point for me is when people start coming to you regularly. So it's more. It's an inbound kind of thing, you know, if I hit my quota, but nobody's coming and asking Me, you know, how I did it, or anything like that, then you might be able to make a few bucks pushing it out to people. But I don't feel like that's the right timing. One of the things that I get into is how everybody knows outbound is hard. It's no different as a consultant or a coach or somebody selling coursework or whatever, so you want to avoid all that. So if I'm a salesperson or I'm a sales leader and all of a sudden I start getting messages and people asking me, hey, tell me about this. How did you do that? On any number of different topics, that, to me is a tipping point where it's like, maybe there's something here, maybe I'm ready to put something together and push something out. John Barrows and I were having this conversation a couple weeks ago and he asked the same question. And I said, when people start coming to you regularly, that's the tipping point, I think.

And what I love about that is too similar advice to people is, are people internally coming. Coming to you?

Yeah.

Like before you're trying to sell it publicly. Is anyone internally coming to you asking for this advice? Because they know you, they see you. Right. They know that day to day. So I love that as a benchmark because I. You're seeing it. I'm seeing it. It's like everyone and their mom is charging now for like these little courses and these little pamphlets and everything else. And it's like they do. They get a little splash and it dies off.

Yeah, that, that part is, is, is tricky. Like, I don't begrudge somebody trying to make a couple dollars, but I think if you're, if you're trying to get into creating and, and consulting and coaching and that kind of thing, I think getting into it to pay off a couple bills or to generate, you know, five figures worth of income or even low six figures. I think that's the wrong way to look at it because going to work for yourself is all of the wonderful things that everybody talks about, but it's also extremely stressful and everything is on you and it's very, very difficult. And a lot of people fail. So pulling the trigger a little bit too soon just because you can make a few bucks. Well, what if you just waited? What if you waited and stored up this knowledge, accumulated this experience and this information, got better at actually coaching people before you sold a coaching course or whatever? What if you got better at writing and before you started selling, you know, writing courses and stuff like that? And this can Take time. But if you delay a little bit and wait until you've got a body of work, consistent body of work, like not. I was a VP of sales one time. Here's how I crushed it. Here's how I was a VP of sales five, six times. Not one time of hitting quota. Here's how I was a AE at such and such place and hit quota four years in a row. Then when you actually finally pull the trigger, I think you got seven figure potential. And that's a difference. A big, big difference. A whole other zero difference that I think a lot of people don't pay enough attention to. I didn't get into consulting to replicate what I could earn in a W2 role. I got into consulting and doing my own thing so I could add a zero on top of it. But if I would have tried to do that after a year or two of experience, I never would have made it.

And I. That, that's the clarifier I was looking for. Because I'm not against someone trying to make a buck. But we're talking about how to generate income. There's a difference, right? You can go out and you can make a buck. You can go out and, you know, sell it and you make five grand one time. But income is consistent. Income is providing that lifestyle that you're looking for. And I agree, it's that delayed gratification. Because also if you've been doing it for four years, and this is, I think where you're going with this next is have you helped other people do the same thing? Because it's one thing if you've hit quota for four years, it's one thing if you led a sales org to hit their number. Have you helped anyone else do it? So how do you recommend people start that process of helping others achieve what they've achieved? Maybe before they're charging for it, maybe before they've created a course, like, okay, people are coming, then what? Like, how do I actually start to help others do this? How do I take what I know and make it repeatable for other people?

Well, I think it 100% should be for free. Just to clarify and be real specific, it shouldn't be. I've done this thing. Now how do I monetize to your point? You know, I think of it like, you know, being a VP of sales or being a professional coach, even in a sport. Think about all the people that were your managers, Kevin, that are now in VP of sales roles now think about how many of them failed. Now think about how Many of them made it. And the delta between those two is a sign of, well, how good is Kevin's like how to build a sales or kind of plan? How good is, is Scott's framework for how to sell if his whole sales organization couldn't hit their, their target? Like, how am I going to go teach people about the addiction model of selling if my own fucking organization couldn't hit their numbers through this framework? How am I going to teach people how to build and scale sales orgs if the people who came up under me couldn't go do it and couldn't go replicate it on their own? But when you've got a handful of people who you've kind of mentored and guided, maybe who worked under you for a little while or alongside of you for a little while, and then they go off on their own and you see them blossom and they keep coming back to you asking for help, hey, what did you do at this juncture? What did you do here? What did you do there? And you guide them. And now all of a sudden, in many cases, they've accomplished as much as you in those roles or even, God forbid, more than you and surpassed you in those roles. Now I think you know that this blueprint framework, whatever you want to call it, really works. Kevin's methodology of selling works, Scott's methodology of building a sales org works. I in building untethered, I've had many conversations with people for free for years. How to create side hustles, when to do it, why to do it, all this kind of thing. So I have people who, when I reach the course, wrote, wrote me or texted me back. And they're like, yo, I've been doing this already, Let me know if you need a testimonial. I'm like, you didn't even need to go through the course because you already went through the course for years. So I get it. And it's just so much more powerful that way. It's a different story to tell. That adds a filter of credibility on top of it, you know, and you can't, you can't fake that.

No, it's, it's other people. And that's what also, I think everyone seems to forget about a brand. A brand is what other people say about you, not what you say about you. It's what other people say. That's your brand. And if other people are saying, this guy's shit works. This guy helped me get here, they helped me achieve X this, like, that's the brand that you want. One of Funny enough, one of my former managers, who's now like a director, head of sales, wants to start doing consulting. And I said like, what's. What's your niche going to be? He's like, I want to help level up managers. I was like, great. How many managers have you leveled up already? He's like, well, what do you mean? I was like, how. How many managers have you leveled up? How many managers can you point to and go, wow, like, I made that person significantly better. And they would say the same thing. Because if you don't have that yet, you need to go get that first.

Right.

As I hopped over to their LinkedIn, I looked at their recommendations. Guess what I didn't see, Scott? Guess. Guess what? I didn't see that.

I know where you're going. I know where you're going.

Any recommendations from managers on their team saying how much they leveled him up? And I said, all right, you need to go get that, because if your own people aren't vouching for how much you've improved them, it's not going to work for other people, too. And so as we keep going down this path. So I'm glad you called us out. That free, right? That free to start, like, just start helping. How long do you do that? Like, okay, so I'm starting to get some inbound. I'm starting to, you know, just help people for free. At what point do you think you start to say, all right, now it's time to start charging for this, and now it's time to start putting together, like, a package or program around this?

Yeah, for me, it was when my time started to get real thin. So I helped people and help people and help people with no real thought of monetizing until all of a sudden, I looked at my calendar one day and I was like, oh, you know, I have no time to go eat lunch or I'm stressed trying to get to this familial stuff that I need to do, household kind of stuff, because I've booked myself to the point where there's no free time in the day. And when I got to that point, I was like, I can't do this anymore. I can't just give away all of my time unless I'm monetizing it. And I have a number of people, any number of people who would now say, like, to your point about brand, to. Would now say, scott will help you sight unseen, doesn't know you, will reply to your messages, take your phone call, da, da, da, da, da. I have enough of reputation out there for being helpful and doing this stuff and enough people who've gone on to succeed that I have to put up a filter to protect my time. And then that filter became. I got to start charging for this. And that number was very, very small initially. I didn't throw a big number up. And you and I argue about this all the time. Even today, I don't throw big numbers around possibly enough. So I threw a small number up that would keep the barrier low to entry. But I felt like, you know, became reasonable for my time and then that got. Felt like, you know, became reasonable for my time and then that got flooded and then I raised the number and then that got flooded and I raised the number and so I just keep raising it right. And that was just how I gave. That was my gauge for am I ready to start kind of, kind of charging for this if I've maxed out helping as many people as I can. But I'm starting to eat into, you know, personal time and, and whatnot. Like, I gotta cut. I gotta cut back a little bit. And one of the ways to cut back a little bit, I thought, well, if I start charging people, it's not going to be 10 out of 10 people who say, yes, it's going to be, you know, three, four, something like that. And that felt like a more reasonable kind of figure for me.

So where did you start, though? Because I think right now, in my opinion, I'm excited to hear yours on this.

I feel like a lot of people.

Have it backwards where everyone's starting with a course, but they haven't done any, like, coaching or consulting. You literally just came out with your first course. Course. You've had books, but that's your first course. You started with coaching and consulting, Right? So talk about that journey there. A little bit of like, okay, you started with coaching and consulting first. Is that your preference? Or if you would do this all over again, would you start with a course and then try to land.

Oh, God, no. Everything I'm all about is like, do all the work first. You can't, you can't do all these shortcuts for, for a lot of different reasons, whether it's credibility or, or expertise in what it is you're teaching or just from a dollars and cents perspective. Like, I'm not here to make six figures, I'm here to make seven figures. Plus, I don't think you can do that if you just show up one day and start releasing courses. So I was an operator. Excuse me, I was an operator for 15 plus years. I don't even know the exact number. I have to sit and think about it. Not just selling, but managing, leading, building and scaling, sales orgs, coaching, training, developing. I started creating, if you will, content regularly in probably 2015, 2016 or so. So maybe six something years ago is my guess. Doing it regularly. So now I'm experimenting with, with writing and being this kind of creator, if you will. I released my book in 2017, my first book. I started doing trainings live, not just like for my team, but for people who don't know me in Costa Rica at surf and sales. So I'm testing sort of my presentation skills, right? My training skills, my ability to gather a crowd or create some kind of micro community. That's 2017, 2020. I start this virtual happy hour with Justin Welsh and then he had to step away. And I've been running it with Amy Volas for two and a half years. I'm fielding questions live on the fly. I don't know where the, where these questions are coming from. I don't know what they are. Like, it's like feeling objections in real time and people are there to hear your answers and your expertise. So I'm working on sort of my presence, if you will, potentially my ability to think on my feet and answer things. I'm listening for themes that keep coming up. One of the themes, themes that always comes up is, hey, I'm thinking about making a move in my career. So that informs content, that informs a direction. But I'm practicing all these things. Then I don't know what year it was. Maybe 2021, maybe you tell me about this thing called Patreon, and I'm like, I'm gonna do that. And like 36 hours later, I launched the thing, which is a whole other funny thing, funny story, but now I'm running a Patreon group where I'm charging a little bit, but I'm creating content, I'm producing content, I'm interviewing people, I'm bringing other people on to my Tequila Tuesday show where other people like yourself are training individuals. I'm watching them train. Like all these things that I've been doing, I've built up to this place where I, I, I feel like I have dabbled in or executed very well any number of these different channels to get yourself untethered and to break away. I've been an individual contributor, I've been a sales manager, I've been a VP of sales. I've been a content creator. I've run live events overseas and domestically and charge people for it. I've run multiple communities. I have trained internally and externally. God knows how many times. I have run small communities and brought other people in to study how they give trainings and deliver trainings. I'm relatively late to the course creation game. I didn't want to do it until.